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7 Travelers rated Chester highly for Small Town and Opera Houses

Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
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Book a package and join the 188 others who’ve received 100% off their flights this year!

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Top Rated Hotels for your Chester Vacation

Holiday Inn Express Hotel & Suites Sparta
Holiday Inn Express Hotel & Suites Sparta
2.5 out of 5.0 1301 N Market St, Sparta, IL
Free Cancellation
4.4/5 (9 reviews)

Everything was clean and the staff was very VERY nice. Just wished the shower had a handheld shower head and a hair dryer.

Reviewed on Jul 22, 2019
Situated in a rural location, this hotel is 1.5 mi (2.5 km) from Misselhorn Art Gallery and 2.4 mi (3.8 km) from Sparta Country Club. Fort Kaskaskia and Fort ...
Best Western Chester Hotel
Best Western Chester Hotel
2.5 out of 5.0 2150 State Street, Chester, IL
Free Cancellation
4.1/5 (8 reviews)

Toilet stoped up never fixed during stay. Small bath room.

Reviewed on Apr 9, 2018
Situated in Chester, this hotel is 0.6 mi (1 km) from Chester Skating Rink and 2.1 mi (3.4 km) from Elzie C. Segar Memorial Park. Mary's River Covered Bridge ...

Tips for planning your Chester vacation

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Chester Vacation Package Deals

Ready to create that ultimate Chester escape? The talented team at Orbitz will bundle your flight and hotel room bookings for the best value.

If you package your bookings, you'll save up to $857*! Simply choose your preferred airfares, hotels, rental cars and experiences.

Along with that, our database lists no less than 500,000 international hotel options and 500 partner airlines. Don't stress out if you have trouble choosing — we'll make it a breeze!

Our package deals will help you create the getaway of your dreams. With endless options to bundle your flights and hotels, the only thing left to do is pack your bags and grab your passport!

Join Orbitz Rewards

Do you want to be rewarded super fast? We've developed a straightforward program — just start booking with us and you'll get instant Orbucks!

Interested in perks, like complimentary breakfast, at all Orbitz Rewards VIP Hotels? Just stay four nights for gold status and 12 nights for platinum status in a full year. And, how do you redeem? It's a piece of cake! You can make use of your Orbitz Rewards points on your very next booking.

Chester Travel Guide

Where is Chester?

Whether you carefully organize every second of your vacation or you don't plan beyond lunch, it's always a good idea to know just where you're going. Ready to learn a little about Chester?

You'll find it approximately 130 miles south of Springfield, the state capital of Illinois, and roughly 16 miles north of Perryville.

9,000 locals live in this part of Southwest Illinois.

Places to Visit in Chester

Slide on the rink and practice your best Olympic skater moves at Chester Skating Rink. Seeking some more options? Not only something that helps us get from A to B, bridges are also often landmarks that add to destination's identity. Take in Mary's River Covered Bridge and find out how, when and why this renowned structure was made. But wait, that's not all there is! Make sure you plan a stop off to discover the captivating exhibitions found at Popeye Museum.

Car Rentals in Chester

Take your love of travel further by checking out car rentals in Chester. No matter where you want to go or what you're in the mood to do, Orbitz will help you find a ride that fits your adventurous spirit.

Nearest Airports to Chester

Lying 40 miles north of Chester's downtown area, MidAmerica-St. Louis Airport (BLV) is where your vacation begins. Once you've grabbed your suitcase from baggage claim, you'll be checking out the attractions of Chester in no time!

Popular Places to Visit Near Chester

Jackson is a favorite of tourists. It can be found 35 miles from Chester, and there's no shortage of things to do. Start uncovering the story of the region at the Lazy L Safari Park. If you're eager to find out more, stop by Litz Park and the Steele Crest Winery too. Cobden is another nearby destination located just 40 miles away. This place features Anna City Park, the Lincoln Heritage Winery and the Rustle Hill Winery.

No Cancellation Fees

You can be confident that whatever the motivation behind canceling your booking, we won't ask for a fee.^ Why not call your airline and hotel and ask if they'll do the same?

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.